Most Helpful Girl

I'm usually all for waiting for him to ask YOU out, but I think in this case it's okay if you ask him out first. I would first confer with your friend first. I would talk with her about who she may feel about you two dating. This way you are taking into account her feelings and how this decision may affect her. Even if she says she is not comfortable with it, I would still go for it. Of course, let her know respectfully that while you love your friendship with her, you would really like to try things out with her brother. Just make sure that if you do get in a relationship with her brother, you don't make her feel any less important to you. Having a boyfriend is already enough of a challenge when balancing your time between them and your friends, but it's even more of one when your boyfriend is also the brother of your close friend. You don't want to cause sibling rivalry over you, haha.

Haha yes!!! All the guys said to ask him out as you can tell!!! I kinda tried to ask him out but he told his friend that he "might" ask me out and I'm still very confused about what that means exactly. It's been over a week since I did but I don't know

If you want, you can wait another week or so, but don't give too much time in between. Sometimes, you just gotta take charge, haha. He might be contemplating it right now and just making sure he's making the right decision. If he said he "might" do so, then there is definitely a possibility that he actually WILL. So, give it a little time and see how things turn out. If they don't, then take matters into your own hands. :)

Okay, you said that his sister is a close friend of yours so why would she want to hold him back? since she is your close friend you should go and ask her, surely there will be some reason for her to hold him back? some fear, some concern? I am just saying.